Novel compound and organic light emitting device using same

Abstract

The present invention provides a novel compound and an organic light emitting device using same.

Description

Novel compounds and organic light-emitting devices using the same

[0001] Cross-citation with related application(s)

[0002] This application claims the benefit of priority to Korean Patent Application No. 10-2023-0163417, filed November 22, 2023, the entire disclosure of which is incorporated herein by reference.

[0003]

[0004] The present invention relates to a novel compound and an organic light-emitting device comprising the same.

[0005] Organic light-emitting diodes (OLEDs) generally refer to the conversion of electrical energy into light energy using organic materials. Organic light-emitting devices utilizing this phenomenon boast a wide viewing angle, excellent contrast, and fast response times, and are actively researched due to their superior brightness, operating voltage, and response speed characteristics.

[0006]

[0007] Organic light-emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

[0008]

[0009] There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices such as the above.

[0010] [Prior Art Literature]

[0011] [Patent Document]

[0012] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

[0013] The present invention relates to a novel compound and an organic light-emitting device comprising the same.

[0014] The present invention provides a compound represented by the following chemical formula 1:

[0015] [Chemical Formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] X1 is independently N or CH, provided that at least one of X1 is N,

[0019] X2 is independently N or CH, provided that at least one of X2 is N,

[0020] Ar1 to Ar4 are each independently substituted or unsubstituted C 6-60 C comprising at least one selected from the group consisting of aryl, or substituted or unsubstituted N, O and S; 2-60 It is heteroaryl,

[0021] At least one of Ar1 to Ar4 is biphenylyl substituted with one or two cyano groups,

[0022] Ar5 and Ar6 are each independently substituted or unsubstituted C 6-20 It's Aryl,

[0023] R1 and R2 are each independently hydrogen or deuterium,

[0024] n and m are each independently integers from 0 to 4, provided that n+m is an integer from 1 to 8,

[0025] The compound represented by the above chemical formula 1 does not contain deuterium or contains one or more deuteriums.

[0026]

[0027] In addition, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by the chemical formula 1.

[0028] The compound represented by the above-described chemical formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can improve efficiency, low operating voltage, and / or lifespan characteristics in the organic light-emitting device. In particular, the compound represented by the above-described chemical formula 1 can be used as a hole injection, hole transport, hole injection and transport, luminescence, electron transport, or electron injection material.

[0029] Figure 1 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4).

[0030] Figure 2 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (7), an electron transport layer (8), and a cathode (4).

[0031] Hereinafter, the present invention will be described in more detail to help understand it.

[0032]

[0033] In this specification, or means a bond that connects to another substituent.

[0034]

[0035] The term "substituted or unsubstituted" as used herein means a group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylphosphine group; or a heterocyclic group containing at least one of N, O, and S atoms, or a substituted or unsubstituted group in which two or more of the above-mentioned substituents are linked. For example, the "substituent linked with two or more substituents" may be a biphenyl group. That is, the biphenyl group can be an aryl group or can be interpreted as a substituent in which two phenyl groups are connected.

[0036]

[0037] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0038]

[0039]

[0040] In the present specification, the ester group may have the oxygen of the ester group replaced by a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto.

[0041]

[0042]

[0043] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0044]

[0045]

[0046] In the present specification, the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc.

[0047]

[0048] In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0049]

[0050] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexetylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, Examples include, but are not limited to, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0051]

[0052] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

[0053]

[0054] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

[0055]

[0056] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[0057]

[0058] In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted, It can be, but is not limited to, the following.

[0059]

[0060] In the present specification, a heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl group, There are, but are not limited to, phenothiazinyl groups and dibenzofuranyl groups.

[0061]

[0062] In this specification, the aryl group among the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the examples of the aryl group described above. In this specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the alkyl group described above. In this specification, the heteroaryl among the heteroarylamine may be applied to the description of the heterocyclic group described above. In this specification, the alkenyl group among the aralkenyl group is the same as the examples of the alkenyl group described above. In this specification, the description of the aryl group described above may be applied to the arylene except that it is a divalent group. In this specification, the description of the heterocyclic group described above may be applied to the heteroarylene except that it is a divalent group. In this specification, the description of the aryl group or the cycloalkyl group described above may be applied to the hydrocarbon ring except that it is not a monovalent group but is formed by combining two substituents. In the present specification, the description of the heterocyclic group described above may be applied, except that the heterocyclic group is not monovalent and is formed by combining two substituents.

[0063]

[0064] In the above chemical formula 1, one or more hydrogens may be replaced with deuterium.

[0065]

[0066] Preferably, Ar1 to Ar4 are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, quinquiphenylyl, sexiphenylyl, nathyl, phenylnaphthyl, naphthylphenyl, -(biphenyl)-(naphthyl), dibenzofuran, dibenzothiophene, 9-phenyl-carbazolyl, carbazol-9-yl, pyridinyl, -(phenyl)-(pyridinyl), benzoxazolyl, benzoimidazolyl, benzothiazolyl, -(phenyl)-(benzoxazolyl), -(phenyl)-(benzoimidazolyl), or -(phenyl)-(benzothiazolyl),

[0067] The above Ar1 to Ar4 are each independently unsubstituted or substituted with one or more deuterium, C 1-5 Haloalkyl, C 1-5 Haloalkoxy, cyano, or C 6-20 It is substituted with aryl.

[0068]

[0069] Preferably, Ar1 to Ar4 are each independently unsubstituted or substituted with one or more deuterium, trifluoromethyl, trifluoromethoxy, cyano, or phenyl.

[0070]

[0071] Preferably, in the definition of Ar1 to Ar4, the biphenylyl substituted with one or two cyano groups is any one selected from the group consisting of: each of which is free of deuterium or contains one or more deuteriums:

[0072]

[0073]

[0074] Preferably, Ar5 and Ar6 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenanthrenyl, pyrenyl, triphenylenyl, or fluoranthenyl,

[0075] The above Ar5 and Ar6 are each independently unsubstituted or substituted with one or more deuterium, C 1-4 Alkyl, C 3-6 Cycloalkyl, cyano, pyridinyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, -(P=O)(C 1-4 alkyl)2, or -(P=O)(C 6-20 It is substituted with aryl)2.

[0076]

[0077] Preferably, Ar5 and Ar6 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenanthrenyl, pyrenyl, triphenylenyl, or fluoranthenyl,

[0078] The above Ar5 and Ar6 are each independently unsubstituted or substituted with one or more deuterium, tert-butyl, cyclohexyl, cyano, pyridinyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, -(P=O)(methyl)2, or -(P=O)(phenyl)2.

[0079]

[0080] Preferably, n+m is an integer from 1 to 4. When n+m is 1, n is 0 and m is 1, or n is 1 and m is 0. When n+m is 2, n is 0 and m is 2, or both n and m are 1, or n is 2 and m is 0. When n+m is 3, n is 0 and m is 3, or n is 1 and m is 2, or n is 2 and m is 1, or n is 3 and m is 0. When n+m is 4, n is 0 and m is 4, or n is 1 and m is 3, or both n and m are 2, or n is 3 and m is 1, or n is 4 and m is 0.

[0081]

[0082] Representative examples of compounds represented by the above chemical formula 1 are as follows:

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] In addition, the present invention provides a method for producing a compound represented by the chemical formula 1 as shown in the following reaction scheme 1.

[0119] [Reaction Formula 1]

[0120]

[0121]

[0122] In the above reaction formula 1, the remaining definitions except for Y1 to Y3 are as described above, and Y1 to Y3 are each independently halogen, more preferably bromo or chloro. More preferably, Y1 is bromo and Y2 is chloro.

[0123]

[0124] Steps 1 and 3 of the above reaction scheme 1 are Suzuki coupling reactions, which are preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. Step 2 of the above reaction scheme 1 is a reaction for replacing a halogen with a reactor for the Suzuki coupling reaction, which is preferably performed in the presence of a palladium catalyst and a base.

[0125]

[0126] The above manufacturing method can be further specified in the manufacturing example described below.

[0127]

[0128] In addition, the present invention provides an organic light-emitting device comprising a compound represented by the above chemical formula 1. For example, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic layer comprises a compound represented by the above chemical formula 1.

[0129]

[0130] The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0131]

[0132] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1. In particular, the compound according to the present invention can be used as a dopant of the light-emitting layer.

[0133]

[0134] Additionally, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by the chemical formula 1.

[0135]

[0136] In addition, the electron transport layer, electron injection layer, or layer performing electron transport and electron injection simultaneously includes a compound represented by the chemical formula 1.

[0137]

[0138] In addition, the organic layer may include a light-emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by the chemical formula 1.

[0139]

[0140] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially laminated on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

[0141]

[0142] Figure 1 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). In such a structure, the compound represented by the chemical formula 1 may be included in the light-emitting layer.

[0143]

[0144] Figure 2 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (7), an electron transport layer (8), and a cathode (4). In this structure, the compound represented by the chemical formula 1 may be included in at least one layer of the hole injection layer, the hole transport layer, the light-emitting layer, and the electron transport layer.

[0145]

[0146] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes a compound represented by the chemical formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0147]

[0148] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on the substrate.

[0149]

[0150] In addition, the compound represented by the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0151]

[0152] In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing an organic layer and an anode material on a substrate starting from a cathode material (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0153]

[0154] For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0155]

[0156] As the anode material, a material having a high work function is generally preferred so that hole injection into the organic layer can be facilitated. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0157]

[0158] The cathode material is preferably a material having a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0159]

[0160] The above-mentioned hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect at the anode, an excellent hole injection effect for the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers such as polyaniline and polythiophene.

[0161]

[0162] The above hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. A hole transport material that can transport holes from the anode or the hole injection layer and transfer them to the light-emitting layer is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0163]

[0164] The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0165]

[0166] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocyclic compound may include, but is not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0167]

[0168] Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and styrylamine compounds are compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0169]

[0170] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer is suitable. A material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are used, and in each case, followed by an aluminum layer or a silver layer.

[0171]

[0172] The above electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents movement of excitons generated in the light-emitting layer to the hole injection layer, and is preferably a compound having excellent thin-film forming ability. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0173]

[0174] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0175]

[0176] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0177]

[0178] In addition, the compound represented by the above chemical formula 1 can be included in an organic solar cell or organic transistor in addition to an organic light-emitting device.

[0179]

[0180] The manufacture of the compound represented by the above chemical formula 1 and the organic light-emitting device containing the same is specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0181]

[0182] [Example]

[0183] Example 1: Preparation of Compound 1

[0184]

[0185] Step 1) Preparation of compound 1-a

[0186] In a nitrogen atmosphere, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine (50 g, 114.9 mmol) and 4-bromo-3-chloro-1,1'-biphenyl (30.7 g, 114.9 mmol) were added to tetrahydrofuran (1000 ml), stirred, and refluxed. Then, potassium carbonate (47.6 g, 344.6 mmol) dissolved in water (48 ml) was added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (4 g, 3.4 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in toluene (1137 ml), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 1-a (45.5 g, yield 80%).

[0187] MS: [MH] = 496.2

[0188]

[0189] Step 2) Preparation of compound 1

[0190] In a nitrogen atmosphere, compound 1-a (50 g, 100.8 mmol) and bis(pinacolato)diboron (25.6 g, 100.8 mmol) were added to 1,4-dioxane (1000 ml), stirred, and refluxed. Then, potassium acetate (64.2 g, 302.4 mmol) was added, stirred sufficiently, and bis(dibenzylideneacetone)palladium(0) (0.6 g, 1 mmol) and dicyclohexylphosphine (0.4 g, 2 mmol) were added. After 7 hours of reaction, the mixture was cooled to room temperature, filtered, and the organic layer was distilled. This was dissolved in chloroform (592 ml), washed twice with water, separated, and anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a white solid compound 1-b (33.7 g, yield 57%).

[0191] MS: [M+H] + = 588.3

[0192]

[0193] Step 3) Preparation of compound 1

[0194] In a nitrogen atmosphere, compound 1-b (50 g, 85.1 mmol) and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (31.4 g, 85.1 mmol) were added to tetrahydrofuran (1000 ml), stirred, and refluxed. Then, potassium carbonate (35.3 g, 255.3 mmol) dissolved in water (35 ml) was added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (2.9 g, 2.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in toluene (1350 mL), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 1 (56 g, yield 83%).

[0195] MS: [M+H] + = 794.3

[0196]

[0197] Example 2: Preparation of Compound 2

[0198]

[0199] In Example 1, compound 2 was prepared using the same method as the method for preparing compound 1, except that 4-bromo-3-chloro-1,1'-biphenyl was changed to 4-bromo-3-chloro-1,1'-biphenyl-2',3',4',5',6'-d5.

[0200] MS: [M+H] + = 799.3

[0201]

[0202] Example 3: Preparation of compound 3

[0203]

[0204] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 3'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1'-biphenyl was converted to 3-bromo-2-chloro-1,1'-biphenyl, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile Compound 3 was prepared using the same method as that for compound 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used.

[0205] MS: [M+H] + = 794.3

[0206]

[0207] Example 4: Preparation of compound 4

[0208]

[0209] In Example 1, compound 4 was prepared by the same method as that for compound 1, except that 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was changed to 2'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was changed to 2-chloro-4,6-diphenylpyrimidine.

[0210] MS: [M+H] + = 793.3

[0211]

[0212] Example 5: Preparation of compound 5

[0213]

[0214] In Example 1, compound 5 was prepared by the same method as that for compound 1, except that 4-bromo-3-chloro-1,1'-biphenyl was changed to 8-(2-bromo-3-chlorophenyl)fluoranthene and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was changed to 2'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile.

[0215] MS: [M+H] + = 918.3

[0216]

[0217] Example 6: Preparation of compound 6

[0218]

[0219] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 4'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1'-biphenyl was converted to 2-(2'-bromo-3'-chloro-[1,1'-biphenyl]-2-yl)naphthalene, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile. Compound 6 was prepared using the same method as that for compound 1, except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine was used.

[0220] MS: [M+H] + = 996.4

[0221]

[0222] Example 7: Preparation of compound 7

[0223]

[0224] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was changed to 3'-(4-([1,1'-biphenyl]-2-yl)-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was changed to 3-(4-chloro-6-(naphthalen-1-yl)-1,3,5-triazin-2-yl)benzonitrile. Compound 7 was prepared using the same manufacturing method as that of compound 1, except that:

[0225] MS: [M+H] + = 945.3

[0226]

[0227] Example 8: Preparation of compound 8

[0228]

[0229] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 9-(4-(dibenzo[b,d]thiophen-1-yl)-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole, 4-bromo-3-chloro-1,1'-biphenyl was converted to 2-(4-bromo-3-chlorophenyl)naphthalene, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile. Compound 8 was prepared using the same method as that for compound 1, except that 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used.

[0230] MS: [M+H] + = 1039.3

[0231]

[0232] Example 9: Preparation of compound 9

[0233]

[0234] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 2'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1'-biphenyl was converted to 1-(4-bromo-3-chlorophenyl)naphthalene, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile Compound 9 was prepared using the same method as that for compound 1, except that 3-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)benzonitrile was used.

[0235] MS: [M+H] + = 869.3

[0236]

[0237] Example 10: Preparation of compound 10

[0238]

[0239] In Example 1, compound 10 was prepared by the same method as the method for preparing compound 1, except that 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was changed to 4'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was changed to 2-chloro-4-phenyl-6-(3-(pyrimidin-4-yl)phenyl)-1,3,5-triazine. It was manufactured.

[0240] MS: [M+H] + = 871.3

[0241]

[0242] Example 11: Preparation of compound 11

[0243]

[0244] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 3'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1'-biphenyl was converted to 3'-bromo-4'-chloro-5',6'-diphenyl-1,1':2',1''-terphenyl, Compound 11 was prepared by the same method as that for compound 1, except that 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was changed to 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0245] MS: [M+H] + = 1022.4

[0246]

[0247] Example 12: Preparation of compound 12

[0248]

[0249] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 3'-(4-([1,1'-biphenyl]-3-yl)-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1'-biphenyl was converted to 3-bromo-4-chloro-1,1'-biphenyl, Compound 12 was prepared using the same method as that for compound 1, except that 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was changed to 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0250] MS: [M+H] + = 996.3

[0251]

[0252] Example 13: Preparation of compound 13

[0253]

[0254] In Example 1, compound 13 was prepared by the same method as that of compound 1, except that 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was changed to 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)-[1,1'-biphenyl]-4-yl)pyridine and 4-bromo-3-chloro-1,1'-biphenyl was changed to 2-(4'-bromo-3'-chloro-[1,1'-biphenyl]-3-yl)benzo[d]thiazole.

[0255] MS: [M+H] + = 1001.3

[0256]

[0257] Example 14: Preparation of compound 14

[0258]

[0259] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 4,6-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)-[1,1'-biphenyl]-3-yl)pyrimidine, 4-bromo-3-chloro-1,1'-biphenyl was converted to 4-(4'-bromo-3'-chloro-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile. Compound 14 was prepared using the same method as that for compound 1, except that 4'-(2-chloro-6-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-carbonitrile was used.

[0260] MS: [M+H] + = 1034.3

[0261]

[0262] Example 15: Preparation of compound 15

[0263]

[0264] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 3'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1'-biphenyl was converted to 3-(3'-bromo-4'-chloro-[1,1'-biphenyl]-3-yl)pyrimidine, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile Compound 15 was prepared using the same method as that for compound 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used.

[0265] MS: [M+H] + = 871.3

[0266]

[0267] Example 16: Preparation of compound 16

[0268]

[0269] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine, 4-bromo-3-chloro-1,1'-biphenyl was converted to (4'-bromo-3'-chloro-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile. Compound 16 was prepared using the same method as that for compound 1, except that 2'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used.

[0270] MS: [M+H] + = 946.3

[0271]

[0272] Example 17: Preparation of compound 17

[0273]

[0274] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 3'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1'-biphenyl was converted to 3'-bromo-4'-chloro-[1,1'-biphenyl]-3,4-dicarbonitrile, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile Compound 17 was prepared using the same method as that for compound 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used.

[0275] MS: [M+H] + = 844.3

[0276]

[0277] Example 18: Preparation of compound 18

[0278]

[0279] In Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazine was converted to 4'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaboralon-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1'-biphenyl was converted to 3'-bromo-4'-chloro-[1,1'-biphenyl]-4-carbonitrile, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile Compound 18 was prepared using the same method as that for compound 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used.

[0280] MS: [M+H] + = 819.3

[0281]

[0282] [Experimental Example]

[0283] Experimental Example 1

[0284] A glass substrate coated with a 1,000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent used was a Fischer Co. product, and the distilled water used was distilled water that had been filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0285]

[0286] On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, the following compounds HAT and HT-A were sequentially vacuum deposited to a thickness of 50 Å and 600 Å, respectively, to form a hole transport layer. On the hole transport layer, the following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to a thickness of 200 Å to form a light emitting layer. On the light emitting layer, the compound 1 prepared in Example 1 and the following compound LiQ were vacuum deposited at a weight ratio of 1:1 to a thickness of 360 Å to form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited to a thickness of 10 Å and aluminum was sequentially deposited to a thickness of 1,000 Å to form a cathode.

[0287]

[0288]

[0289] In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 5 x 10 -8 ~ 1 x 10 -7 Torr was maintained, and an organic light-emitting device was fabricated.

[0290]

[0291] Experimental examples 2 to 18

[0292] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound in Table 1 below was used instead of Compound 1.

[0293]

[0294] Comparative Experimental Examples 1 and 2

[0295] An organic light-emitting device was manufactured in the same manner as Experimental Example 1, except that the compounds in Table 1 below were used instead of Compound 1. Compounds ET1 and ET2 used in Table 1 below were as follows.

[0296]

[0297]

[0298] For the organic light-emitting device manufactured above, 10 mA / cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA / cm 2 The time (T90) at which the initial luminance reaches 90% of the current density was measured. The results are shown in Table 1 below.

[0299] Compound (electron injection and transport layer) voltage (V@10mA / cm 2 )Efficiency (cd / A@10mA / cm 2 )Color coordinates (x,y)T90(hr@20mA / cm 2)Experimental Example 1 Compound 14.09 5.55 (0.136, 0.112) 145Experimental Example 2 Compound 24.03 5.62 (0.136, 0.111) 165Experimental Example 3 Compound 34.01 5.55 (0.136, 0.112) 175Experimental Example 4 Compound 44.58 5.78 (0.136, 0.111) 195Experimental Example 5 Compound 54.10 5.65 (0.136, 0.111) 148Experimental Example 6 Compound 64.26 5.75 (0.136, 0.111) 211Experimental Example 7 Compound 74.13 5.69 (0.136, 0.112) 195Experimental Example 8 Compound 84.145.59(0.136, 0.111)182 Experimental example 9 Compound 94.255.58(0.136, 0.112)157 Experimental example 10 Compound 104.255.68(0.136, 0.111)168 Experimental example 11 Compound 114.305.45(0.136, 0.111)203 Experimental example 12 Compound 124.405.58(0.136, 0.111)192 Experimental example 13 Compound 134.155.68(0.136, 0.111)162 Experimental example 14 Compound 144.025.62(0.136, 0.112)202Experimental Example 15 Compound 154.135.74(0.136, 0.111)195Experimental Example 16 Compound 164.255.02(0.136, 0.111)182Experimental Example 17 Compound 174.615.13(0.136, 0.111)152Experimental Example 18 Compound 184.455.29(0.136, 0.111)168Comparative Experimental Example 1 Compound ET15.752.62(0.136, 0.111)10Comparative Experimental Example 2 Compound ET24.353.20(0.136, 0.111)32

[0300]

[0301] As described in Table 1 above, it was confirmed that the organic light-emitting device using the compound represented by Chemical Formula 1 of the present invention exhibited excellent characteristics in voltage, efficiency, and lifespan.

[0302]

[0303] Specifically, compounds 1 to 16 used in Experimental Examples 1 to 16 are directly connected to a biphenyl group that is ortho-linked between two 6-membered heterocyclic groups containing at least one N, thereby smoothly controlling electron mobility. In addition, since an aryl group is substituted on the biphenyl linker, structural distortion occurs, which is advantageous for electron transport. In addition, at least one of Ar1 to Ar4 includes a biphenyl group substituted with one or two cyano groups, thereby smoothly controlling electron injection and transport characteristics. Therefore, it was confirmed that compounds 1 to 16 used in Experimental Example 1 had superior characteristics in terms of voltage, efficiency, and lifespan.

[0304]

[0305] In addition, it was confirmed that compounds 17 and 18 used in Experimental Examples 17 and 18 can improve the efficiency and lifespan characteristics of organic light-emitting devices compared to Comparative Example 2 used in Comparative Experimental Example 2 in which a cyano group is directly substituted in the linker by introducing a cyano group substituted in an aryl group in the biphenyl linker to smoothly control electron injection and transfer.

[0306] [Explanation of symbols]

[0307] 1: Substrate 2: Anode

[0308] 3: Emitting layer 4: Cathode

[0309] 5: Hole injection layer 6: Hole transport layer

[0310] 7: Emitting layer 8: Electron transport layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 are each independently N or CH, and only X 1 At least one of them is N, X 2 are each independently N or CH, and only X 2 At least one of them is N, Ar 1 Inland Ar 4 are each independently substituted or unsubstituted C 6-60 C comprising at least one selected from the group consisting of aryl, or substituted or unsubstituted N, O and S; 2-60 It is heteroaryl, Just Ar 1 Inland Ar 4 At least one of them is biphenylyl substituted with one or two cyano groups, Ar 5 and Ar 6 are each independently substituted or unsubstituted C 6-20 It's Aryl, R 1 and R 2 are each independently hydrogen or deuterium, n and m are each independently an integer from 0 to 4, provided that n+m is an integer from 1 to 8, The compound represented by the above chemical formula 1 does not contain deuterium or contains one or more deuterium atoms.

2. In paragraph 1, Ar 1 Inland Ar 4 are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, quinquiphenylyl, sexiphenylyl, nathyl, phenylnaphthyl, naphthylphenyl, -(biphenyl)-(naphthyl), dibenzofuran, dibenzothiophene, 9-phenyl-carbazolyl, carbazol-9-yl, pyridinyl, -(phenyl)-(pyridinyl), benzoxazolyl, benzoimidazolyl, benzothiazolyl, -(phenyl)-(benzoxazolyl), -(phenyl)-(benzoimidazolyl), or -(phenyl)-(benzothiazolyl), Above Ar 1 Inland Ar 4 are each independently unsubstituted or substituted with one or more deuterium, C 1-5 Haloalkyl, C 1-5 Haloalkoxy, cyano, or C 6-20 substituted with aryl, compound.

3. In paragraph 2, Ar 1 Inland Ar 4 are each independently unsubstituted or substituted with one or more deuterium, trifluoromethyl, trifluoromethoxy, cyano, or phenyl, compound.

4. In paragraph 1, Ar 1 Inland Ar 4 In the definition, biphenylyl substituted with one or two cyano is any one selected from the group consisting of: The following are each free of deuterium or containing one or more deuterium: compound.

5. In paragraph 1, Ar 5 and Ar 6 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenanthrenyl, pyrenyl, triphenylenyl, or fluoranthenyl, Above Ar 5 and Ar 6 are each independently unsubstituted or substituted with one or more deuterium, C 1-4 Alkyl, C 3-6 Cycloalkyl, cyano, pyridinyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, -(P=O)(C 1-4 alkyl) 2 , or -(P=O)(C 6-20 Aryl) 2 Replaced with, compound.

6. In paragraph 1, n+m is an integer between 1 and 4, compound.

7. In paragraph 1, The compound represented by the above chemical formula 1 is one selected from the group consisting of: compound:

8. An organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 7.

9. In paragraph 8, The organic layer containing the above compound is an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons. Organic light emitting diode.

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